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Villas in Key West

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Featured Villas in Key West

Old Town Garden Villas
3.5 out of 5
921 Center St, Key West, FL
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Located in Key West Historic District, this villa is within a 5-minute walk of Duval Street and Ernest Hemingway Home and Museum. South Beach and Key West Butterfly ...

4.7/5Exceptional! (3 reviews)

"Very clean very well updated and remodeled great layout and love the quiet respite just 1-2 blocks off Duval so super convenient to everything - we just walked everywhere!"…"

Reviewed on Mar 11, 2020

Old Town Garden Villas
Secret Villa I @ Old Town With Private Pool, Close to Duval!

Located in Key West Historic District, this historic villa is steps from Nancy Forrester's Secret Garden and Duval Street. Mallory Square and Ernest Hemingway ...

5/5Exceptional! (48 reviews)
Family Weekend

"Property was perfect for a family weekend, thanks so much!!"…"

Reviewed on Mar 14, 2020

Secret Villa I @ Old Town With Private Pool, Close to Duval!
Secret Villa II @ Old Town: With Private Pool, Close to Duval!

Located in Key West Historic District, this historic villa is steps from Nancy Forrester's Secret Garden and Duval Street. Mallory Square and Ernest Hemingway ...

No reviews
Didn't want to leave!

"Excellent location, beautiful property. Would stay again."…"

Reviewed on Mar 14, 2020

Secret Villa II @ Old Town: With Private Pool, Close to Duval!
A++ Location in Down Town Key West w/ 2 Pools, Huge Private Roof Deck & Parking

Located in Key West Historic District, this historic villa is steps from San Carlos Institute - Casa Cuba and Duval Street. Ernest Hemingway Home and Museum ...

No reviews
premier property in key west

"We rented 519 and 522 Bahama street from Feb 29 th thru March 8 th for our families for the week of our wedding in Key West . Mark has done an outstanding job with these properties. Both properties were extremely modern and clean and our families loved staying at them. We would highly recommend these ..."…"

Reviewed on Mar 16, 2020

A++ Location in Down Town Key West w/ 2 Pools, Huge Private Roof Deck & Parking
Key West Escapes - Luxury Yoga Vacations
4 out of 5
Tropical Street, Key West, FL
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Located in White Street Gallery District, this villa is within a 15-minute walk of Higgs Beach and Duval Street. South Beach and Smathers Beach are also within ...

Key West Escapes - Luxury Yoga Vacations
Shark Key Chateau Apartment 5
4 out of 5
79 Cannon Royal Drive, Key West, FL
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Nestled on the beach, this Key West villa is Shark Key and 2.6 mi (4.1 km) from Rockland Key. Boca Chica Beach and Boca Chica Nude Beach are also within 6 mi ...

Shark Key Chateau Apartment 5
Downtown Duval Street Penthouse- Private Pool-parking-roof Deck- Walk Everywhere

Located in Key West Historic District, this villa is steps from San Carlos Institute - Casa Cuba and Duval Street. Ernest Hemingway Home and Museum and Harry ...

No reviews
Great Stay

"We overall enjoyed our stay here. The owner was very proactive in our needs. The bar next door was loud on the weekend but overall we had a great time!"…"

Reviewed on Feb 19, 2020

Downtown Duval Street Penthouse- Private Pool-parking-roof Deck- Walk Everywhere
6 bdrm Duval Compound -Old Town Key West
4 out of 5
519 Duval Street, Key West, FL
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Located in Key West Historic District, this villa is steps from San Carlos Institute - Casa Cuba and Duval Street. Ernest Hemingway Home and Museum and Harry ...

6 bdrm Duval Compound -Old Town Key West
Duval Penthouse
4 out of 5
519 Duval Street, # 201, Key West, FL
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Located in Key West Historic District, this villa is steps from San Carlos Institute - Casa Cuba and Duval Street. Ernest Hemingway Home and Museum and Harry ...

Duval Penthouse
Bahamas House
4 out of 5
522 Bahama Street, Key West, FL
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Located in Key West Historic District, this villa is steps from San Carlos Institute - Casa Cuba and Duval Street. Ernest Hemingway Home and Museum and Harry ...

Bahamas House
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Key West

Oceans Edge Key West Resort, Hotel & Marina
Oceans Edge Key West Resort, Hotel & Marina
4 out of 5
5950 Peninsular Avenue, Key West, FL
$259
per night
May 3 - May 4
4.5/5Wonderful! (2,563 reviews)

"Beautiful property with great service and amenities! We loved kayaking, paddleboarding, kid's movie, nice resaurant and wonderful pool area. My family really enjoyed their stay and we will definitely be going back on our next visit to Key West."…"

Reviewed on Mar 24, 2020

Oceans Edge Key West Resort, Hotel & Marina
24 North Hotel Key West
24 North Hotel Key West
4 out of 5
3820 North Roosevelt Boulevard, Key West, FL
$199
per night
May 3 - May 4
4.1/5Very Good! (2,097 reviews)

"Great staff member, Ron, was very helpful at the front desk!"…"

Reviewed on Mar 27, 2020

24 North Hotel Key West
Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
$449
per night
May 4 - May 5
4.4/5Excellent! (5,405 reviews)

"Beautiful place to stay. Their swimming pools are amazing, the staff is incredible."…"

Reviewed on Mar 20, 2020

Southernmost Beach Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Vacation Like a Royal in a Key West Villa

One of the most important parts of planning a vacation is deciding where you're going to stay. Usually, no matter where you go, there will always be a hotel, resort, or motel. But when you stay in Key West, you have the opportunity to upgrade from the typical trip and try something new: your very own private villa. You could have a pool, lawn, kitchen, bar, and lounge area all to yourself, rather than sharing a public resort area with all the other visitors. We're here to help you make the most of your holiday, so go on, kick back and live like royalty. When you stay at one of Expedia's Key West villas, you can let all those troubles of lodging at a hotel melt away as you enjoy the privacy of your own estate. That is the kind of freedom we know you like, especially if you can share the cost with a few close friends or your family. Book a gorgeous villa with us, so we can get you a marvelous place to stay that you will be talking about for years to come.

Stay in a Key West Villa for Your Next Trip

Renting a Key West villa can be a great substitute to staying at a resort in Key West as a family or with a group. You will surely treasure the experience of immersing yourself in the local culture and community. If you'd rather take a secluded getaway without the touristy crowds, we can help set you up with a private villa. If you're intrigued by the idea of a villa rental but are a bit daunted by the process, stick with Expedia, and we will help you make your plans as easy as possible. After you experience all the charm and the benefits of spending your holiday in a private luxurious villa, you won't want to go back to the traditional resort.

Book Your Villa With Expedia Today

Ditch the noisy resorts and cramped suites year by booking a villa when you vacation in Key West. They will give you more privacy and space, so you can come and go as often as you please. You'll have tons of space and time to make new memories and talk with your loved ones on this huge property, all while enjoying the conveniences of a luxury villa. From cooking in the kitchen to playing in the pool, you'll be excited to see that the possibilities are limitless after you step inside your Key West villa. What are you waiting for? Book today and save big-time on one of our holiday villas.